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Wentibianthrone A

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Bianthrone

Canonical Smiles	OC[C@@H](COC(=O)c1c(C)cc2c(c1O)C(=O)c1c([C@H]2[C@H]2c3cc(C)cc(c3C(=O)c3c2cc(OC)cc3O)O)cc(cc1O)O)O
InChI	InChI=1S/C35H30O12/c1-13-4-18-26(21-9-17(46-3)10-24(41)30(21)33(43)28(18)22(39)5-13)27-19-6-14(2)25(35(45)47-12-16(38)11-36)32(42)31(19)34(44)29-20(27)7-15(37)8-23(29)40/h4-10,16,26-27,36-42H,11-12H2,1-3H3/t16-,26-,27-/m0/s1
InChIKey	YDKPGQXHCPSPPY-BLHYWNLJSA-N
Formula	C₃₅H₃₀O₁₂
HBA	12
HBD	7
MW	642.61
Rotatable Bonds	6
TPSA	211.28
LogP	3.4
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	47
Formal Charge	0
Fraction CSP3	0.23
Exact Mass	642.17
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus wentii	Trichocomaceae	Fungi	5066

Showing of synonyms

Form I.C, Bonus M, et al. (2019). Xanthone, benzophenone and bianthrone derivatives from the hypersaline lake-derived fungus Aspergillus wentii. Bioorg Med Chem,2019,27(20),115005. [View] [PubMed]

Pubchem: 146682320

Nmrshiftdb2: 70067118

Chembl: CHEMBL4444028

No compound-protein relationship available.

SMILES: c1cccc(C2=O)c1C(c(c23)cccc3)C(c(c45)cccc5)c6c(C4=O)cccc6

Level: 1

Mol. Weight: 642.61 g/mol

SMILES: c1cccc(c12)Cc3c(C2=O)cccc3

Level: 0

Mol. Weight: 642.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.3
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.04
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 57.74

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.03
Plasma Protein Binding: 82.61
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 7.55
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.19
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.94
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.09
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Toxic
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -103607.9
Rat (Acute): 2.43
Rat (Chronic Oral): 4.69
Fathead Minnow: 148.85
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 4044.33
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 3.19
Log(P): 5.95
Log S: -5.99
Log(Vapor Pressure): -208.67
Melting Point: 254.22
pKa Acid: 7.13
pKa Basic: 4.94

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9178
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9028
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8991
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8659
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8619
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8182
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7977
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7973
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7848
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7837
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7730
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7540
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7473
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7467
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7338
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7333
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7304
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7287
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7229
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7198
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7197
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7165
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7109
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7073
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7019

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